metal-organic compounds
Chlorido(chlorodifluoroacetato-κO)bis(1,10-phenanthroline-κ2N,N′)manganese(II)
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
The chloride and chlorodifluoroacetate anions occupy cis positions in the octahedral coordination geometry of the title compound, [Mn(C2ClF2O2)Cl(C12H8N2)2]. The two N-heterocycles both chelate the metal atom.
Related literature
For isostructural chlorido(1,10-phenanthroline)(trichloroacetato)manganese(II), see: Chen et al. (2006).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).
Supporting information
10.1107/S1600536808010829/sg2236sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808010829/sg2236Isup2.hkl
Manganese dichloride dihydrate (0.5 g, 3 mmol) was dissolved in ethanol and chlorodifluoroacetic acid (0.3 ml, 3 mol) was added. The mixture was heated briefly, after which 1,10-phenanthroline (1.6 g, 6 mmol) was added. The solution when allowed to cool yielded yellow crystals.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 Å) and were included in the
in the riding model approximation, with U(H) set to 1.2Ueq(C).Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).Fig. 1. 70% Probability thermal ellipsoid plot (Barbour, 2001) of Mn(C12H8N2)2(C2ClF2O2)Cl. Hydrogen atoms are drawn as spheres of arbitrary radii. |
[Mn(C2ClF2O2)Cl(C12H8N2)2] | F(000) = 1172 |
Mr = 580.27 | Dx = 1.566 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2908 reflections |
a = 16.8822 (4) Å | θ = 2.3–21.4° |
b = 10.3781 (3) Å | µ = 0.80 mm−1 |
c = 14.8364 (5) Å | T = 100 K |
β = 108.813 (2)° | Irregular block, yellow |
V = 2460.5 (1) Å3 | 0.20 × 0.15 × 0.10 mm |
Z = 4 |
Bruker SMART APEX diffractometer | 5628 independent reflections |
Radiation source: fine-focus sealed tube | 3863 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.104 |
ω scans | θmax = 27.5°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −21→21 |
Tmin = 0.856, Tmax = 0.924 | k = −13→13 |
30077 measured reflections | l = −19→14 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0868P)2] where P = (Fo2 + 2Fc2)/3 |
5628 reflections | (Δ/σ)max = 0.001 |
334 parameters | Δρmax = 1.00 e Å−3 |
0 restraints | Δρmin = −0.63 e Å−3 |
[Mn(C2ClF2O2)Cl(C12H8N2)2] | V = 2460.5 (1) Å3 |
Mr = 580.27 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.8822 (4) Å | µ = 0.80 mm−1 |
b = 10.3781 (3) Å | T = 100 K |
c = 14.8364 (5) Å | 0.20 × 0.15 × 0.10 mm |
β = 108.813 (2)° |
Bruker SMART APEX diffractometer | 5628 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3863 reflections with I > 2σ(I) |
Tmin = 0.856, Tmax = 0.924 | Rint = 0.104 |
30077 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.04 | Δρmax = 1.00 e Å−3 |
5628 reflections | Δρmin = −0.63 e Å−3 |
334 parameters |
x | y | z | Uiso*/Ueq | ||
Mn1 | 0.28449 (3) | 0.63507 (5) | 0.17308 (4) | 0.02130 (16) | |
Cl1 | 0.33600 (5) | 0.60920 (8) | 0.03799 (6) | 0.0247 (2) | |
Cl2 | 0.21097 (8) | 1.04489 (11) | 0.29372 (9) | 0.0536 (3) | |
F1 | 0.09738 (14) | 1.0724 (2) | 0.1347 (2) | 0.0545 (8) | |
F2 | 0.22337 (14) | 1.0904 (2) | 0.13132 (18) | 0.0402 (6) | |
O1 | 0.24710 (14) | 0.8334 (2) | 0.15829 (18) | 0.0264 (6) | |
O2 | 0.10701 (14) | 0.8221 (2) | 0.1178 (2) | 0.0330 (6) | |
N1 | 0.17254 (16) | 0.5061 (3) | 0.1004 (2) | 0.0240 (6) | |
N2 | 0.21023 (16) | 0.6109 (3) | 0.2757 (2) | 0.0230 (6) | |
N3 | 0.39971 (15) | 0.7160 (3) | 0.2897 (2) | 0.0219 (6) | |
N4 | 0.36197 (16) | 0.4637 (3) | 0.2525 (2) | 0.0215 (6) | |
C1 | 0.1249 (2) | 0.4714 (3) | 0.1547 (3) | 0.0239 (7) | |
C2 | 0.1524 (2) | 0.4572 (3) | 0.0131 (3) | 0.0275 (8) | |
H2 | 0.1857 | 0.4800 | −0.0254 | 0.033* | |
C3 | 0.0848 (2) | 0.3739 (3) | −0.0250 (3) | 0.0338 (9) | |
H3 | 0.0720 | 0.3432 | −0.0885 | 0.041* | |
C4 | 0.0376 (2) | 0.3369 (3) | 0.0295 (3) | 0.0312 (9) | |
H4 | −0.0080 | 0.2793 | 0.0049 | 0.037* | |
C5 | 0.0572 (2) | 0.3857 (3) | 0.1237 (3) | 0.0279 (8) | |
C6 | 0.0103 (2) | 0.3542 (3) | 0.1854 (3) | 0.0328 (9) | |
H6 | −0.0356 | 0.2963 | 0.1638 | 0.039* | |
C7 | 0.0297 (2) | 0.4050 (4) | 0.2738 (3) | 0.0313 (9) | |
H7 | −0.0018 | 0.3813 | 0.3140 | 0.038* | |
C8 | 0.0975 (2) | 0.4944 (3) | 0.3072 (3) | 0.0266 (8) | |
C9 | 0.1187 (2) | 0.5535 (3) | 0.3974 (3) | 0.0294 (8) | |
H9 | 0.0885 | 0.5332 | 0.4397 | 0.035* | |
C10 | 0.1829 (2) | 0.6399 (3) | 0.4236 (3) | 0.0316 (8) | |
H10 | 0.1973 | 0.6819 | 0.4836 | 0.038* | |
C11 | 0.2276 (2) | 0.6658 (3) | 0.3604 (3) | 0.0248 (7) | |
H11 | 0.2724 | 0.7257 | 0.3795 | 0.030* | |
C12 | 0.14495 (19) | 0.5264 (3) | 0.2484 (3) | 0.0228 (7) | |
C13 | 0.45711 (19) | 0.6274 (3) | 0.3381 (2) | 0.0217 (7) | |
C14 | 0.4167 (2) | 0.8390 (3) | 0.3096 (3) | 0.0274 (8) | |
H14 | 0.3766 | 0.9014 | 0.2767 | 0.033* | |
C15 | 0.4910 (2) | 0.8821 (3) | 0.3767 (3) | 0.0299 (8) | |
H15 | 0.5006 | 0.9716 | 0.3891 | 0.036* | |
C16 | 0.5496 (2) | 0.7935 (3) | 0.4243 (3) | 0.0282 (8) | |
H16 | 0.6007 | 0.8210 | 0.4696 | 0.034* | |
C17 | 0.5338 (2) | 0.6622 (3) | 0.4060 (3) | 0.0251 (8) | |
C18 | 0.5921 (2) | 0.5629 (3) | 0.4517 (3) | 0.0291 (8) | |
H18 | 0.6446 | 0.5861 | 0.4962 | 0.035* | |
C19 | 0.5738 (2) | 0.4374 (3) | 0.4329 (3) | 0.0280 (8) | |
H19 | 0.6135 | 0.3737 | 0.4643 | 0.034* | |
C20 | 0.4951 (2) | 0.3985 (3) | 0.3662 (3) | 0.0241 (7) | |
C21 | 0.4724 (2) | 0.2692 (3) | 0.3466 (3) | 0.0271 (8) | |
H21 | 0.5097 | 0.2025 | 0.3778 | 0.033* | |
C22 | 0.3961 (2) | 0.2393 (3) | 0.2822 (3) | 0.0284 (8) | |
H22 | 0.3795 | 0.1520 | 0.2689 | 0.034* | |
C23 | 0.3430 (2) | 0.3395 (3) | 0.2362 (3) | 0.0249 (8) | |
H23 | 0.2906 | 0.3178 | 0.1909 | 0.030* | |
C24 | 0.43732 (19) | 0.4937 (3) | 0.3181 (2) | 0.0211 (7) | |
C25 | 0.1748 (2) | 0.8752 (3) | 0.1456 (2) | 0.0234 (7) | |
C26 | 0.1740 (2) | 1.0211 (3) | 0.1694 (3) | 0.0330 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.0192 (3) | 0.0265 (3) | 0.0161 (3) | −0.00035 (19) | 0.0028 (2) | −0.0001 (2) |
Cl1 | 0.0231 (4) | 0.0310 (4) | 0.0189 (5) | 0.0005 (3) | 0.0053 (3) | 0.0006 (3) |
Cl2 | 0.0682 (7) | 0.0614 (7) | 0.0398 (7) | −0.0225 (6) | 0.0291 (6) | −0.0250 (5) |
F1 | 0.0351 (12) | 0.0376 (13) | 0.086 (2) | 0.0129 (10) | 0.0131 (13) | 0.0026 (13) |
F2 | 0.0446 (13) | 0.0359 (12) | 0.0427 (16) | −0.0083 (10) | 0.0178 (11) | 0.0021 (11) |
O1 | 0.0224 (12) | 0.0323 (13) | 0.0221 (14) | 0.0033 (9) | 0.0038 (10) | 0.0028 (10) |
O2 | 0.0236 (12) | 0.0375 (14) | 0.0354 (17) | −0.0043 (10) | 0.0061 (12) | −0.0090 (12) |
N1 | 0.0213 (13) | 0.0294 (15) | 0.0185 (16) | 0.0014 (11) | 0.0024 (12) | −0.0009 (12) |
N2 | 0.0199 (13) | 0.0282 (15) | 0.0185 (16) | 0.0015 (11) | 0.0028 (12) | 0.0013 (12) |
N3 | 0.0200 (13) | 0.0265 (15) | 0.0174 (16) | −0.0022 (11) | 0.0036 (12) | 0.0019 (11) |
N4 | 0.0207 (13) | 0.0280 (15) | 0.0158 (16) | −0.0024 (11) | 0.0057 (12) | −0.0013 (11) |
C1 | 0.0208 (15) | 0.0279 (17) | 0.0204 (19) | 0.0042 (13) | 0.0032 (14) | 0.0028 (14) |
C2 | 0.0279 (17) | 0.0340 (19) | 0.017 (2) | −0.0003 (14) | 0.0022 (15) | −0.0027 (15) |
C3 | 0.034 (2) | 0.037 (2) | 0.024 (2) | −0.0029 (16) | 0.0000 (17) | −0.0069 (16) |
C4 | 0.0240 (17) | 0.0299 (19) | 0.032 (2) | −0.0014 (14) | −0.0015 (16) | −0.0027 (16) |
C5 | 0.0242 (17) | 0.0295 (18) | 0.025 (2) | 0.0015 (14) | 0.0017 (15) | −0.0007 (15) |
C6 | 0.0222 (17) | 0.035 (2) | 0.037 (2) | −0.0039 (14) | 0.0042 (17) | 0.0015 (17) |
C7 | 0.0267 (18) | 0.037 (2) | 0.033 (2) | 0.0002 (15) | 0.0130 (17) | 0.0044 (17) |
C8 | 0.0221 (16) | 0.0308 (18) | 0.025 (2) | 0.0011 (14) | 0.0044 (15) | 0.0028 (15) |
C9 | 0.0291 (18) | 0.040 (2) | 0.020 (2) | 0.0007 (15) | 0.0101 (16) | 0.0041 (16) |
C10 | 0.0336 (19) | 0.040 (2) | 0.020 (2) | 0.0023 (16) | 0.0070 (16) | −0.0016 (16) |
C11 | 0.0225 (16) | 0.0343 (18) | 0.0140 (18) | −0.0009 (13) | 0.0009 (14) | −0.0014 (14) |
C12 | 0.0177 (15) | 0.0279 (17) | 0.0197 (19) | 0.0032 (13) | 0.0018 (14) | 0.0015 (14) |
C13 | 0.0211 (15) | 0.0271 (17) | 0.0172 (18) | −0.0006 (13) | 0.0067 (14) | 0.0018 (14) |
C14 | 0.0259 (17) | 0.0265 (18) | 0.028 (2) | −0.0006 (13) | 0.0063 (16) | 0.0005 (15) |
C15 | 0.0263 (17) | 0.0292 (18) | 0.030 (2) | −0.0073 (14) | 0.0042 (16) | −0.0041 (16) |
C16 | 0.0240 (16) | 0.0343 (19) | 0.024 (2) | −0.0074 (14) | 0.0048 (15) | −0.0008 (15) |
C17 | 0.0229 (16) | 0.0341 (19) | 0.0187 (19) | −0.0043 (14) | 0.0071 (15) | 0.0009 (15) |
C18 | 0.0202 (16) | 0.037 (2) | 0.025 (2) | −0.0021 (14) | 0.0003 (15) | −0.0001 (16) |
C19 | 0.0235 (16) | 0.0338 (19) | 0.022 (2) | 0.0043 (14) | 0.0014 (15) | 0.0031 (15) |
C20 | 0.0209 (16) | 0.0340 (18) | 0.0159 (18) | 0.0020 (14) | 0.0042 (14) | 0.0017 (14) |
C21 | 0.0263 (17) | 0.0274 (18) | 0.026 (2) | 0.0048 (14) | 0.0061 (15) | 0.0028 (15) |
C22 | 0.0268 (17) | 0.0271 (18) | 0.028 (2) | 0.0018 (14) | 0.0047 (15) | 0.0000 (15) |
C23 | 0.0213 (16) | 0.0295 (18) | 0.023 (2) | −0.0012 (13) | 0.0055 (15) | 0.0006 (14) |
C24 | 0.0206 (15) | 0.0303 (17) | 0.0134 (17) | 0.0002 (13) | 0.0070 (13) | 0.0025 (13) |
C25 | 0.0224 (16) | 0.0364 (19) | 0.0107 (17) | 0.0001 (14) | 0.0045 (14) | 0.0008 (14) |
C26 | 0.0266 (17) | 0.037 (2) | 0.035 (2) | 0.0007 (15) | 0.0089 (17) | −0.0015 (17) |
Mn1—O1 | 2.143 (2) | C7—C8 | 1.432 (5) |
Mn1—N1 | 2.283 (3) | C7—H7 | 0.9500 |
Mn1—N2 | 2.277 (3) | C8—C12 | 1.401 (5) |
Mn1—N3 | 2.305 (3) | C8—C9 | 1.410 (5) |
Mn1—N4 | 2.295 (3) | C9—C10 | 1.363 (5) |
Mn1—Cl1 | 2.443 (1) | C9—H9 | 0.9500 |
Cl2—C26 | 1.764 (4) | C10—C11 | 1.405 (5) |
F1—C26 | 1.339 (4) | C10—H10 | 0.9500 |
F2—C26 | 1.355 (4) | C11—H11 | 0.9500 |
O1—C25 | 1.250 (4) | C13—C17 | 1.407 (5) |
O2—C25 | 1.217 (4) | C13—C24 | 1.436 (4) |
N1—C2 | 1.330 (5) | C14—C15 | 1.400 (5) |
N1—C1 | 1.358 (5) | C14—H14 | 0.9500 |
N2—C11 | 1.324 (5) | C15—C16 | 1.368 (5) |
N2—C12 | 1.363 (4) | C15—H15 | 0.9500 |
N3—C14 | 1.321 (4) | C16—C17 | 1.398 (5) |
N3—C13 | 1.361 (4) | C16—H16 | 0.9500 |
N4—C23 | 1.331 (4) | C17—C18 | 1.436 (5) |
N4—C24 | 1.365 (4) | C18—C19 | 1.346 (5) |
C1—C5 | 1.403 (5) | C18—H18 | 0.9500 |
C1—C12 | 1.440 (5) | C19—C20 | 1.435 (5) |
C2—C3 | 1.398 (5) | C19—H19 | 0.9500 |
C2—H2 | 0.9500 | C20—C21 | 1.399 (5) |
C3—C4 | 1.362 (6) | C20—C24 | 1.410 (4) |
C3—H3 | 0.9500 | C21—C22 | 1.369 (5) |
C4—C5 | 1.422 (5) | C21—H21 | 0.9500 |
C4—H4 | 0.9500 | C22—C23 | 1.398 (5) |
C5—C6 | 1.428 (6) | C22—H22 | 0.9500 |
C6—C7 | 1.353 (6) | C23—H23 | 0.9500 |
C6—H6 | 0.9500 | C25—C26 | 1.556 (5) |
O1—Mn1—N1 | 110.1 (1) | C9—C10—C11 | 119.0 (4) |
O1—Mn1—N2 | 88.1 (1) | C9—C10—H10 | 120.5 |
O1—Mn1—N3 | 82.9 (1) | C11—C10—H10 | 120.5 |
O1—Mn1—N4 | 153.8 (1) | N2—C11—C10 | 123.3 (3) |
O1—Mn1—Cl1 | 101.1 (1) | N2—C11—H11 | 118.4 |
N1—Mn1—N2 | 72.6 (1) | C10—C11—H11 | 118.3 |
N1—Mn1—N3 | 159.7 (1) | N2—C12—C8 | 122.5 (3) |
N1—Mn1—N4 | 92.1 (1) | N2—C12—C1 | 117.2 (3) |
N1—Mn1—Cl1 | 90.4 (1) | C8—C12—C1 | 120.2 (3) |
N2—Mn1—N3 | 93.0 (1) | N3—C13—C17 | 122.6 (3) |
N2—Mn1—N4 | 85.2 (1) | N3—C13—C24 | 117.8 (3) |
N2—Mn1—Cl1 | 162.7 (1) | C17—C13—C24 | 119.7 (3) |
N3—Mn1—N4 | 72.2 (1) | N3—C14—C15 | 123.2 (3) |
N3—Mn1—Cl1 | 102.6 (1) | N3—C14—H14 | 118.4 |
N4—Mn1—Cl1 | 92.4 (1) | C15—C14—H14 | 118.4 |
C25—O1—Mn1 | 126.1 (2) | C16—C15—C14 | 119.0 (3) |
C2—N1—C1 | 117.6 (3) | C16—C15—H15 | 120.5 |
C2—N1—Mn1 | 126.6 (2) | C14—C15—H15 | 120.5 |
C1—N1—Mn1 | 115.7 (2) | C15—C16—C17 | 119.6 (3) |
C11—N2—C12 | 117.9 (3) | C15—C16—H16 | 120.2 |
C11—N2—Mn1 | 125.9 (2) | C17—C16—H16 | 120.2 |
C12—N2—Mn1 | 116.0 (2) | C16—C17—C13 | 117.6 (3) |
C14—N3—C13 | 117.9 (3) | C16—C17—C18 | 123.3 (3) |
C14—N3—Mn1 | 126.2 (2) | C13—C17—C18 | 119.1 (3) |
C13—N3—Mn1 | 115.8 (2) | C19—C18—C17 | 121.3 (3) |
C23—N4—C24 | 117.7 (3) | C19—C18—H18 | 119.3 |
C23—N4—Mn1 | 126.4 (2) | C17—C18—H18 | 119.3 |
C24—N4—Mn1 | 115.8 (2) | C18—C19—C20 | 121.0 (3) |
N1—C1—C5 | 123.3 (3) | C18—C19—H19 | 119.5 |
N1—C1—C12 | 117.9 (3) | C20—C19—H19 | 119.5 |
C5—C1—C12 | 118.7 (3) | C21—C20—C24 | 117.9 (3) |
N1—C2—C3 | 123.3 (4) | C21—C20—C19 | 123.0 (3) |
N1—C2—H2 | 118.4 | C24—C20—C19 | 119.1 (3) |
C3—C2—H2 | 118.4 | C22—C21—C20 | 119.7 (3) |
C4—C3—C2 | 119.5 (4) | C22—C21—H21 | 120.2 |
C4—C3—H3 | 120.3 | C20—C21—H21 | 120.2 |
C2—C3—H3 | 120.3 | C21—C22—C23 | 118.9 (3) |
C3—C4—C5 | 119.2 (3) | C21—C22—H22 | 120.6 |
C3—C4—H4 | 120.4 | C23—C22—H22 | 120.6 |
C5—C4—H4 | 120.4 | N4—C23—C22 | 123.5 (3) |
C1—C5—C4 | 117.0 (3) | N4—C23—H23 | 118.2 |
C1—C5—C6 | 119.8 (4) | C22—C23—H23 | 118.2 |
C4—C5—C6 | 123.1 (3) | N4—C24—C20 | 122.3 (3) |
C7—C6—C5 | 121.4 (3) | N4—C24—C13 | 117.9 (3) |
C7—C6—H6 | 119.3 | C20—C24—C13 | 119.8 (3) |
C5—C6—H6 | 119.3 | O2—C25—O1 | 131.3 (3) |
C6—C7—C8 | 120.3 (4) | O2—C25—C26 | 116.1 (3) |
C6—C7—H7 | 119.9 | O1—C25—C26 | 112.5 (3) |
C8—C7—H7 | 119.9 | F1—C26—F2 | 106.1 (3) |
C12—C8—C9 | 117.8 (3) | F1—C26—C25 | 112.2 (3) |
C12—C8—C7 | 119.5 (3) | F2—C26—C25 | 111.7 (3) |
C9—C8—C7 | 122.7 (3) | F1—C26—Cl2 | 108.6 (3) |
C10—C9—C8 | 119.5 (4) | F2—C26—Cl2 | 107.7 (2) |
C10—C9—H9 | 120.3 | C25—C26—Cl2 | 110.3 (3) |
C8—C9—H9 | 120.3 | ||
N2—Mn1—O1—C25 | −45.9 (3) | C12—C8—C9—C10 | 1.0 (5) |
N1—Mn1—O1—C25 | 24.8 (3) | C7—C8—C9—C10 | −178.5 (3) |
N4—Mn1—O1—C25 | −121.0 (3) | C8—C9—C10—C11 | −1.4 (5) |
N3—Mn1—O1—C25 | −139.1 (3) | C12—N2—C11—C10 | 0.9 (5) |
Cl1—Mn1—O1—C25 | 119.4 (3) | Mn1—N2—C11—C10 | −175.2 (2) |
O1—Mn1—N1—C2 | 96.7 (3) | C9—C10—C11—N2 | 0.4 (5) |
N2—Mn1—N1—C2 | 178.0 (3) | C11—N2—C12—C8 | −1.3 (5) |
N4—Mn1—N1—C2 | −97.7 (3) | Mn1—N2—C12—C8 | 175.2 (2) |
N3—Mn1—N1—C2 | −135.8 (3) | C11—N2—C12—C1 | 177.6 (3) |
Cl1—Mn1—N1—C2 | −5.3 (3) | Mn1—N2—C12—C1 | −5.9 (4) |
O1—Mn1—N1—C1 | −87.0 (2) | C9—C8—C12—N2 | 0.4 (5) |
N2—Mn1—N1—C1 | −5.7 (2) | C7—C8—C12—N2 | 179.9 (3) |
N4—Mn1—N1—C1 | 78.7 (2) | C9—C8—C12—C1 | −178.5 (3) |
N3—Mn1—N1—C1 | 40.5 (4) | C7—C8—C12—C1 | 1.0 (5) |
Cl1—Mn1—N1—C1 | 171.1 (2) | N1—C1—C12—N2 | 0.7 (4) |
O1—Mn1—N2—C11 | −66.0 (3) | C5—C1—C12—N2 | −179.0 (3) |
N1—Mn1—N2—C11 | −177.7 (3) | N1—C1—C12—C8 | 179.7 (3) |
N4—Mn1—N2—C11 | 88.6 (3) | C5—C1—C12—C8 | 0.0 (5) |
N3—Mn1—N2—C11 | 16.7 (3) | C14—N3—C13—C17 | −1.5 (5) |
Cl1—Mn1—N2—C11 | 171.2 (2) | Mn1—N3—C13—C17 | 174.8 (3) |
O1—Mn1—N2—C12 | 117.8 (2) | C14—N3—C13—C24 | 178.3 (3) |
N1—Mn1—N2—C12 | 6.1 (2) | Mn1—N3—C13—C24 | −5.3 (4) |
N4—Mn1—N2—C12 | −87.6 (2) | C13—N3—C14—C15 | 0.8 (5) |
N3—Mn1—N2—C12 | −159.4 (2) | Mn1—N3—C14—C15 | −175.1 (3) |
Cl1—Mn1—N2—C12 | −5.0 (4) | N3—C14—C15—C16 | 0.3 (6) |
O1—Mn1—N3—C14 | −6.1 (3) | C14—C15—C16—C17 | −0.8 (6) |
N2—Mn1—N3—C14 | −93.8 (3) | C15—C16—C17—C13 | 0.1 (5) |
N1—Mn1—N3—C14 | −137.4 (3) | C15—C16—C17—C18 | 179.2 (4) |
N4—Mn1—N3—C14 | −177.8 (3) | N3—C13—C17—C16 | 1.1 (5) |
Cl1—Mn1—N3—C14 | 93.7 (3) | C24—C13—C17—C16 | −178.8 (3) |
O1—Mn1—N3—C13 | 177.9 (2) | N3—C13—C17—C18 | −178.1 (3) |
N2—Mn1—N3—C13 | 90.2 (2) | C24—C13—C17—C18 | 2.1 (5) |
N1—Mn1—N3—C13 | 46.6 (4) | C16—C17—C18—C19 | 179.0 (4) |
N4—Mn1—N3—C13 | 6.1 (2) | C13—C17—C18—C19 | −1.9 (6) |
Cl1—Mn1—N3—C13 | −82.3 (2) | C17—C18—C19—C20 | 0.0 (6) |
O1—Mn1—N4—C23 | 159.6 (3) | C18—C19—C20—C21 | −178.0 (4) |
N2—Mn1—N4—C23 | 83.7 (3) | C18—C19—C20—C24 | 1.7 (5) |
N1—Mn1—N4—C23 | 11.4 (3) | C24—C20—C21—C22 | 0.2 (5) |
N3—Mn1—N4—C23 | 178.4 (3) | C19—C20—C21—C22 | 179.9 (4) |
Cl1—Mn1—N4—C23 | −79.1 (3) | C20—C21—C22—C23 | 1.0 (6) |
O1—Mn1—N4—C24 | −25.2 (4) | C24—N4—C23—C22 | −0.3 (5) |
N2—Mn1—N4—C24 | −101.0 (2) | Mn1—N4—C23—C22 | 174.8 (3) |
N1—Mn1—N4—C24 | −173.4 (2) | C21—C22—C23—N4 | −1.0 (6) |
N3—Mn1—N4—C24 | −6.4 (2) | C23—N4—C24—C20 | 1.6 (5) |
Cl1—Mn1—N4—C24 | 96.1 (2) | Mn1—N4—C24—C20 | −174.1 (3) |
C2—N1—C1—C5 | 1.2 (5) | C23—N4—C24—C13 | −178.2 (3) |
Mn1—N1—C1—C5 | −175.5 (2) | Mn1—N4—C24—C13 | 6.1 (4) |
C2—N1—C1—C12 | −178.5 (3) | C21—C20—C24—N4 | −1.5 (5) |
Mn1—N1—C1—C12 | 4.8 (4) | C19—C20—C24—N4 | 178.8 (3) |
C1—N1—C2—C3 | 0.7 (5) | C21—C20—C24—C13 | 178.3 (3) |
Mn1—N1—C2—C3 | 176.9 (3) | C19—C20—C24—C13 | −1.4 (5) |
N1—C2—C3—C4 | −1.8 (5) | N3—C13—C24—N4 | −0.5 (5) |
C2—C3—C4—C5 | 1.0 (5) | C17—C13—C24—N4 | 179.3 (3) |
N1—C1—C5—C4 | −1.8 (5) | N3—C13—C24—C20 | 179.7 (3) |
C12—C1—C5—C4 | 177.9 (3) | C17—C13—C24—C20 | −0.5 (5) |
N1—C1—C5—C6 | 180.0 (3) | Mn1—O1—C25—O2 | −18.7 (6) |
C12—C1—C5—C6 | −0.3 (5) | Mn1—O1—C25—C26 | 161.9 (2) |
C3—C4—C5—C1 | 0.7 (5) | O2—C25—C26—F1 | −14.5 (5) |
C3—C4—C5—C6 | 178.8 (3) | O1—C25—C26—F1 | 164.9 (3) |
C1—C5—C6—C7 | −0.2 (5) | O2—C25—C26—F2 | −133.6 (3) |
C4—C5—C6—C7 | −178.3 (3) | O1—C25—C26—F2 | 45.9 (4) |
C5—C6—C7—C8 | 1.2 (5) | O2—C25—C26—Cl2 | 106.7 (3) |
C6—C7—C8—C12 | −1.6 (5) | O1—C25—C26—Cl2 | −73.8 (3) |
C6—C7—C8—C9 | 177.9 (3) |
Experimental details
Crystal data | |
Chemical formula | [Mn(C2ClF2O2)Cl(C12H8N2)2] |
Mr | 580.27 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 16.8822 (4), 10.3781 (3), 14.8364 (5) |
β (°) | 108.813 (2) |
V (Å3) | 2460.5 (1) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.80 |
Crystal size (mm) | 0.20 × 0.15 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.856, 0.924 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 30077, 5628, 3863 |
Rint | 0.104 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.165, 1.04 |
No. of reflections | 5628 |
No. of parameters | 334 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.00, −0.63 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).
Mn1—O1 | 2.143 (2) | Mn1—N3 | 2.305 (3) |
Mn1—N1 | 2.283 (3) | Mn1—N4 | 2.295 (3) |
Mn1—N2 | 2.277 (3) | Mn1—Cl1 | 2.443 (1) |
O1—Mn1—N1 | 110.1 (1) | N1—Mn1—Cl1 | 90.4 (1) |
O1—Mn1—N2 | 88.1 (1) | N2—Mn1—N3 | 93.0 (1) |
O1—Mn1—N3 | 82.9 (1) | N2—Mn1—N4 | 85.2 (1) |
O1—Mn1—N4 | 153.8 (1) | N2—Mn1—Cl1 | 162.7 (1) |
O1—Mn1—Cl1 | 101.1 (1) | N3—Mn1—N4 | 72.2 (1) |
N1—Mn1—N2 | 72.6 (1) | N3—Mn1—Cl1 | 102.6 (1) |
N1—Mn1—N3 | 159.7 (1) | N4—Mn1—Cl1 | 92.4 (1) |
N1—Mn1—N4 | 92.1 (1) |
Acknowledgements
The authors thank the University of Malaya for funding this study (grant No. SF022155/2007A) and also for the purchase of the diffractometer.
References
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, L., Wang, X.-W., Chen, F.-P., Chen, Y. & Chen, J.-Z. (2006). Acta Cryst. E62, m1743–m1745. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar
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Manganese dichloride typically reacts with carboxylate anions in the presence of a neutral α,α-dimine ligand (such as 1,10-phenanthroline) to furnish the expected manganese dicarboxylate as the 1:2 adduct of the N-heterocycle. In the case of the reaction with the trichloroacetate anion, only one chloride is displaced. Chlorido-bis(1,10-phenanthroline)(trichloroacetato)manganese exists as a monomeric compound; the crystal structure displays π–π interactions that appear to stabilize the structure (Chen et al., 2006). Replacing the trichloroacetate anion by the chlorodifluoroacetate anion furnishes an isostructural compound (Scheme I, Fig. 1).